Process for improving cellulose textile materials and product thereof



United States Patent PROCESS FOR IMPROVING CELLULOSE TEXTILE MATERIALS AND PRODUCT THEREOF Bruno v. Reihnitz, Mannheim-Feudcnheim, and Wilhelm Ruemens and Kurt Eeideck, Ludwigshafen (Rhine), Germany, assiguors to Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen (Rhine), Germany No Drawing. Application August 16, 1952, Serial No. 304,842

Claims priority, application Germany August 18, 1951 12 Claims. (Cl. 117-64) This invention relates to a process for improving cellulose textile materials by impregnating with methylol compounds of 4,5-dihydroxyimidazolidone and to cellulose textile materials thus treated.

For improving cellulose fibres it is advantageous to use methylol compounds of low-molecular nitrogenous compounds having the following grouping:

or their initial materials.

These compounds, either on the surface of or within the interior of the fibres, are converted into resinous condensation products in the presence of acids or acid-react ing compounds, preferably at elevated temperatures.

We have now found that creaseproof and waterproof impregnations can be prepared on textiles on the basis of natural or regenerated cellulose by treating the textiles with solutions of methylol compounds of 4,5-dihydroxyimidazolidone in the presence of acid-reacting hardening catalysts, as for example acids, acid-reacting salts or potentially acid compounds (i. e. compounds which react acid when heated or in the presence of methylol compounds, as for example ammonium salts).

Suitable 4,5 dihydroxyimidazoline of which the methylol compounds may be employed according to this invention, are for example the 4,5-dihydroxyimidazolidone of the following constitution:

KOCH-NH /C=X KOCH-NH (in which X represents 0, S or NH) and also the 4,5- dihydroxyimidazolidones of diacetyl, benzil and the like, in general monoureins of a-fi-dicarbonyl compounds.

By methylol compounds we mean the addition products of 1 or 2 mols of formaldehyde to 1 mol of a monourein, or the water-soluble initial condensation products of these substances, or mixtures of the addition products and the initial condensation products. Description of the methylol compounds is set forth in greater detail in the application of Von Reibnitz, et al., Serial No. 304,841, filed August 16, 1952.

in order to carry out the process, the textile material is preferably impregnated with an aqueous solution of the methylol compounds and the hardening catalyst, dried, for example at 40 to 85 C., and then heated for a short time at a higher temperature, preferably at from 110 to 140 C.

According to another modification of the process, the methylol compounds may be produced from the 4,5-dihydroxyimidazolidones and formaldehyde on the fibres and then hardened. Methylol compounds of other lowmolecular substances which form aminoplasts, as for example of urea, urethanes or melamine, or the said aminoplast-forming substances and formaldehyde may be added during the impregnation. It is also possible to add during the impregnation polyfunctional compounds having reactive hydrogen atoms which are capable of reacting with the methylol-4,5-dihydroxyimidazolidones to form resinous condensation products. Such compounds are for example glycols, amino alcohols and diamines.

The treated textiles are characterized by good resistance to creasing, increased resistance to shrinkage and wet tearing and reduced swelling value. It is especially remarkable that they have a higherabrasion resistance than textiles treated with methylol compounds of urea.

There is no unpleasant odour during the carrying out of the process, and the treated goods are also unobjectionable from the point of view of odour. The bath stability is also very good even after the addition of the hardening catalyst.

According to a further modification of the process, waterproof coatings and waterproof embossed effects can be prepared on textiles. For this purpose the textiles are impregnated with a solution of the methylol compounds of 4,S-dihydroxyimidazolidones and dried, for example at 40 to C. The textiles are then calendered or embossed, with or without friction, at about to 150 C. under high pressure whereby at the same time a glossy and embossed effect are obtained. They are then heated for 5 to 10 minutes at higher temperatures, preferably at to C. The textiles become waterproof by the treatment and acquire a chintz finish.

In order to increase the waterproof glossy effect, in particular with staple fibre fabrics, there may be added to the solutions of the methylol-4,S-dihydroxyimidazolidones at the same time finishing agents, as for example high-molecular polyglycol ethers, polyvinyl pyrrolidone, poly acrylic acid and derivatives thereof, polyvinyl imidazole, saponificaticn products of polyacrylonitrile or polyacrylic acid esters, polyvinyl alcohol, soluble starch, dextrine, or cellulose ethers or esters also animal glue and amides obtained by the reaction of long-chain aliphatic carboxylic acids and aminoalcohols.

The following examples will further illustrate this invention but the invention is not restricted to these ex amples. The parts are by weight.

Example 1 120 to 140 parts of the dimethylol-4,5-dihydroxyimidazolidone are dissolved in 1000 parts of water and 20 to 25 parts of zinc chloride are added. A staple fibre fabric is impregnated with this liquor, squeezed out and dried at 70 C. The fabric is thenheated for 5 minutes at 120 C. After this treatment it has a very good creaseproof effect which is stable to Washing. The swelling value is reduced by about 45 per cent.

Example 2 4 parts of ammonium chloride are added to 1000 parts of an 8 per cent aqueous solution of an initial condensation product from the 4,S-dihydroxyimidazolidone and formaldehyde (molecular ratio 1:2). There is then added an emulsion of 30 parts of a paraifin wax mixture containing zirconium or aluminium hydroxide in 100 parts :of water. A cotton fabric is impregnated with thismix ture, squeezed out and dried at 70 C. The fabric is then gcalendered under pressure at 120 C. and then heated for minutes at 130 C.

The fabric acquires a chintz-like coating with a glossy effect which is stable to water.

Example 4 Example 5 160 parts of dimethylol-4,5-dihydroxyimidazolidone and 56 parts of ethyleneglycol are dissolved together with 4 parts of diammonium phosphate in 1000 parts of water. A staple fibre fabric is impregnated with this liquor, squeezed out, dried at 70 C. and then heated for 5 minutes at 170 C. The fabric thus treated has a creaseproof efiect which is stable to water and has a reduced swelling value.

Example 6 120 parts of the dimethylol-4,S-dihydroxyimidazolidone and 42 parts of ethylene glycol are dissolved in 900 parts of water. parts of polyvinyl alcohol and 5 parts of ammonium nitrate and 0.5 part of sodium bicarbonate or acetate in 100 parts of water are added to the solution. A staple fibre fabric is impregnated with this liquor, squeezed out and dried. It is then calendered l to 3 times under high pressure at 120 C. and then heated for '5 minutes at 130 C. The fabric acquires a washable coating with a glossy effect which is stable to water.

What we claim is:

1. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution .of a methylol compound of a 4,5- dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, drying and heating then the impregnated textiles to harden the impregnating agent em- 'ployed.

2. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, drying and heating then the impregnated textiles to harden the impregnating agent employed.

3. A process as claimed in claim 2 wherein dimethylol- 4,S-dihydroxyimidazolidone is used.

4. A process as claimed in claim 2 wherein monomethylol-4,S-dihydroxyimidazolidone is used. 7

5. A process as claimed in claim 2 wherein the methylol compounds of 4,S-dihydroxyimidazolidone are prepared in the textiles from glyoxal monourein and formaldehyde.

6. A process as claimed in claim 2 wherein methylol compounds of aminoplast-forming substances selected from the class consisting of urea, urethanes and melamine are also added.

7. A process as claimed in claim alcohols are also added.

8. A process as claimed in claim 2 wherein waterrepellent substances are also added.

9. A process as claimed in claim 2 wherein finishing agents are also added.

10. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-di hydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, calandering the impregnated textiles after drying and heating then the textiles to harden the impregnating agent.

11. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, calendering the impregnated fabric after drying to a temperature from C. to 150 C. and heating then the textiles to a temperature from C. to C. to harden the impregnating agent.

12. Cellulose textiles having an impregnation of a hardened methylol compound of 4,5-dihydroxyimidazolidone.

2 wherein polyhydric References Cited in the file of this patent UNITED STATES PATENTS 2,504,857 MacIntyre Apr. 18, 1950 2 ,574,114 Lehmann Nov. 6, 1951 2,588,640 Lehmann Mar. 11, 1952 

1. A PROCESS FOR THE PRODUCTION OF IMPREGNATIONS ON CELLULOSE TEXTILES WHICH COMPRISES IMPREGNATING THE TEXTILES WITH A SOLUTION OF A METHYLOL COMPOUND OF A 4,5DIHYDROXYIMIDAZOLIDONE IN THE PRESENCE OF AN ACID REACTING HARDENING CATALYST, DRYING AND HEATING THEN THE IMPREGNATED TEXTILES TO HARDEN THE IMPREGNATING AGENT EMPLOYED. 